37 Cute & Comfy Back to School Outfits to Copy

Can you believe it’s already back-to-school season?

Time to trade those lazy summer days for some fresh, school outfits that’ll have you looking on point from day one.

I remember my high school days like they were yesterday (okay, maybe not that long ago, but still).

Every year, I’d spend hours planning the perfect first-day of school in high school outfit, trying to balance looking effortlessly cool while making a killer impression.

Trust me, I’ve been through all the trends – from the awkward attempts at preppy chic to the cringey yet iconic emo phase.

But hey, every misstep was a lesson learned, and now I’m here to share all the do’s and don’ts so you can slay your back-to-school looks with zero stress.

Let’s dive into some lit outfit ideas that’ll have you serving major looks and feeling confident AF!

Summer School Outfits

Just because it’s the end of summer doesn’t mean you can’t look absolutely fab while hitting the books.

I remember those first few weeks of school being hot, sweaty and unbreathable. So I learned to dress for that occasion.

The key to nailing your summer school outfits is finding that sweet spot between staying cool in the heat and keeping your style too.

First things first, breathable fabrics are your best friend.

Fabrics lke cotton, linen, and light blends that let your skin breathe.

A cute sundress or a pair of high-waisted shorts with a flowy tank top can be both comfy and chic.

Don’t forget to accessorize with some fun jewelry like bag charms or a trendy belt to add that extra flair.

Footwear is crucial, too.

Opt for sandals, Birkenstocks, or slip-on sneakers that are both stylish and practical for those long walks between classes.

And hey, if your school allows it, a wide-brimmed hat or a stylish cap can keep the sun out of your eyes while making you look effortlessly cool.

Layering is another pro tip.

Classrooms can get chilly, so bring a lightweight cardigan or a denim jacket that you can easily throw on and off.

It’s all about being prepared and looking cute no matter the temperature.

Finally, don’t forget your bag.

A stylish tote or backpack not only carries all your essentials but also completes your look. Pick one in a fun color or pattern to really stand out.

Remember, summer school is the perfect opportunity to experiment with your style and try new trends.

So, let’s check out these back to school outfits for summer.

1. Jean Jacket + Wrap Skirt, Tank & White Sneakers

Such a cute and compfy school outfit idea!

Pair a jean jacket with a wrap skirt for a cute and casual look.

Add a simple tank top and finish with classic white sneakers.

This combo is perfect for staying stylish and comfortable, whether you’re heading to class or hanging out with friends.

2. Gingham Shorts + Cute Jean Vest and White Oversized T-Shirt with Birkenstocks

Try pairing gingham shorts with a cute jean vest over a white oversized T-shirt for a trendy summer look.

Complete the outfit with classic Birkenstocks for all-day comfort. This ensemble is ideal for a relaxed day at school, effortlessly combining style with a laid-back vibe.

3. Mini Sun Dress + Tank & Comfy Sneakers

Love this look!

Opt for a mini sundress layered over a tank for a cute and breezy look.

Pair it with comfy sneakers for a perfect blend of style and comfort. This outfit is great for some summer schooling, keeping you cool and stylish all day long.

4. Cotton Shorts + Oversized Top + Sneakers

You can’t go wrong with this comfy back to school outfit.

Cotton shorts paired with an oversized top create a relaxed and stylish summer school outfit.

Match them with sneakers for a perfect mix of comfort and casual flair.

This combination is ideal for everything from gong to school to hanging out with friends, keeping you cool and trendy throughout the hot days.

5. Tennis Pleated Skirt + Oversized Crop Top or Top

Combine a tennis pleated skirt with an oversized crop top for a chic and sporty look.

The flowy skirt adds a touch of elegance, while the crop top keeps it casual.

This outfit is perfect for a day at school, balancing comfort and style effortlessly.

6. Biker Shorts + Jean Jacket + Tank and White Sneakers

Biker shorts paired with a jean jacket create a trendy and functional outfit. Add a tank top underneath for a layered look.

Complete the ensemble with white sneakers for a sporty yet chic look.

This combination is perfect for a casual school day out, providing both comfort and effortless style.

7. Western Oversized T-Shirt (+Thin Lace Sleeve Top) + Jean Shorts + Cowboy Boots

Rock a Western oversized T-shirt with classic jean shorts for a cool, laid-back style.

Add a lacy sleeved top if you want for a more dynamic look.

Complete the look with cowboy boots to add a touch of country flair.

This outfit is perfect for summer school days or casual outings, combining comfort and trendiness.

The mix of oversized and fitted pieces ensures you stay stylish and relaxed all day long.

8. Oversized Button Down + Jean Shorts + Birkenstocks

Pair an oversized button-down with jean shorts for a relaxed yet stylish look for school in the summer days.

Add Birkenstocks for effortless comfort. This outfit is ideal for casual school time, blending a touch of sophistication with laid-back vibes.

9. Crop Tank + Cardigan + Jeans + Sneakers

A crop tank paired with a cardigan offers a stylish yet practical back-to-school outfit.

Match it with your favorite jeans for a comfortable and trendy look.

Complete the ensemble with sneakers for an effortless, casual vibe. This combination keeps you both cozy and fashionable throughout the school day.

10. Crop T-Shirt + Wide-Legged Pants + Platform Sandals

Start your summer school days with a crop T-shirt paired with wide-legged pants for a breezy, stylish look.

Add platform sandals to elevate the outfit.

This combination keeps you cool and comfortable while maintaining a trendy, relaxed vibe perfect for warm-weather school days.

First Day of School Outfits (for High School)

The first day of high school is all about making a statement and setting the tone for the year ahead.

Whether you’re a freshman or a senior, your outfit can boost your confidence and showcase your unique style.

Here are some tips and outfit ideas to help you slay your first day of school look.

Start with the basics: comfort and confidence.

You want to feel good in what you’re wearing.

Consider a pair of well-fitted jeans – they’re versatile and always in style.

Pair them with a trendy top like a crop top or a graphic tee.

Layering is key, especially if your school’s air conditioning is on full blast.

A lightweight cardigan or a denim jacket can add both style and function.

For those who prefer skirts or dresses, a flowy sundress paired with a jean jacket and sneakers offers a perfect blend of cute and casual. If skirts are more your vibe, a pleated skirt with a tucked-in blouse and ankle boots can make a chic statement.

Accessories can make or break an outfit.

A stylish backpack, some layered necklaces, or a stack of bracelets can add that extra flair.

Don’t forget about your shoes – whether you choose classic white sneakers, comfy flats, or trendy boots, make sure they complement your outfit and are comfortable for a day of walking around school.

Finally, don’t shy away from expressing your personality through your clothes.

Whether you’re into bold prints, minimalist designs, or vintage vibes, your first day of school outfit is an opportunity to let your true self shine.

Remember, confidence is your best accessory, so wear it proudly and have a fantastic first day!

11. Soccer Shirt + Track Pants

A soccer shirt paired with track pants creates a sporty and comfortable back-to-school outfit.

This look is perfect for active students who want to stay stylish while being ready for any physical activity. Add some sporty sneakers to complete the ensemble, blending practicality with a trendy athletic vibe.

12. Crop T-Shirt + Jeans + Skate Shoes

For a more skater look, opt for a crop T-shirt paired with jeans for a casual and stylish back-to-school outfit.

Add a pair skate shoes for a laid-back, cool vibe. This combination is perfect for comfort and fashion, making you feel confident and trendy throughout the school day.

13. Ripped White Jeans + Black Top + Converse Shoes

Start your school day with ripped white jeans paired with a sleek black top for a stylish contrast.

Add classic Converse shoes to complete the edgy yet casual look.

This outfit strikes a perfect balance between trendy and comfortable, making it ideal for navigating the halls with confidence and flair.

13. Green Zipped Up Hoodie + Yoga Pants + Sneakers

A classic back to school comfy outfit for sure!

Choose a green zipped-up hoodie paired with yoga pants for a cozy and stylish back-to-school outfit.

Add comfortable sneakers to keep you ready for an active day.

This ensemble combines practicality with style, ensuring you stay warm and trendy while tackling your school day with confidence and ease.

14. Graphic T-Shirt + White Shorts

Pair a graphic T-shirt with white shorts for a cool and casual look. This combination is ideal for staying stylish and comfortable during warm school days.

Add some sneakers for a laid-back, trendy back to school look.

15. Striped Sweater + Jeans + Sneakers

A striped sweater paired with jeans creates a timeless and stylish back-to-school outfit.

Complete the look with sneakers for added comfort and a casual touch.

This combination is perfect for cooler days, providing warmth while keeping you trendy. It’s an effortless way to stay fashionable and comfortable throughout your school day.

16. Cropped V-Neck Top + Sweat Pants

Wear a cropped V-neck top with sweatpants for a stylish yet comfortable back-to-school outfit.

This mix of casual comfort and trendy edge is ideal for a relaxed look.

Finish the ensemble with sneakers to stay both comfortable and fashionable throughout the school day.

17. Long Sleeved Shirt + Sundress + Platform Sneakers

Layer a long-sleeved shirt under a sundress for a stylish back-to-school outfit.

This combination adds a touch of sophistication while keeping things playful.

Pair it with platform sneakers to elevate the look. Perfect for transitioning between seasons, this outfit ensures comfort and style throughout your school day.

18. V-Neck Long Sleeve Sweater + Floral Skirt

A V-neck long sleeve sweater pairs perfectly with a floral skirt for a chic back-to-school outfit.

This combination balances cozy and stylish elements. Ideal for cooler days, it keeps you warm while maintaining a feminine and fashionable look throughout the school day.

19. Cardigan + Sun Dress + Sneakers

Pair a cardigan with a sundress and sneakers for a cozy, stylish back-to-school outfit that’s both comfortable and trendy.

20. Cute Top + Ripped Jeans + Platform Converse

Combine a cute top with ripped jeans for a stylish, casual look.

Add platform Converse to elevate the outfit. This trendy combination is perfect for a laid-back yet fashionable back-to-school style.

Everyday Outfits for Back to School

Navigating through the school year in style doesn’t have to be a challenge.

Everyday outfits that blend comfort and fashion are key to making your back-to-school wardrobe both functional and trendy. For a casual yet cool look, pairing jeans with a graphic tee is always a win.

This combination, finished with sneakers or ankle boots, offers a laid-back yet stylish vibe. On chilly days, an oversized sweater with leggings becomes the perfect cozy yet chic outfit. Slip-on shoes or comfy boots complete this look, ensuring warmth and fashion.

For those who love a mix of feminine and casual styles, a skirt with a simple top and a denim jacket is ideal.

Flats or low-heeled boots add the finishing touch, making this outfit versatile and perfect for transitioning between seasons. When comfort is a top priority, a hoodie with joggers fits the bill.

This athletic-inspired ensemble is both trendy and practical, paired with sneakers for a complete athleisure look that’s perfect for busy school days.

A casual dress with sneakers offers an effortless way to stay stylish.

Whether it’s a sundress or a shirt dress, this combination is easy to wear and ideal for warmer days. By mixing and matching these pieces, you can create a variety of everyday outfits perfect for back to school.

Remember, confidence is your best accessory, so wear what makes you feel great!

21. Turtleneck + Sweatshirt + Jeans + Converse

For that everyday school outfit, pair a turtleneck with a sweatshirt and jeans for a cozy, layered look.

Complete the outfit with Converse sneakers for a stylish and comfortable back-to-school ensemble.

22. Baby Tee + Black Leggings + Gingham Fleece Jacket

For an everyday look at school, try a baby tee with black leggings for a sleek look.

Stay warm and stylish with a gingham fleece jacket, creating the perfect trendy back-to-school outfit.

23. Straight Ripped Jeans + Crop Tee + Sneakers

Try wearing straight ripped jeans with a crop tee for an effortlessly cool look. Add sneakers to complete this casual and trendy back-to-school outfit, ensuring both comfort and style.

24. Cute Cardigan + Tank Top + Jean Skirt + Sneakers

A cute cardigan over a tank top with a jean skirt and sneakers creates a stylish, comfortable back-to-school outfit.

25. Sweatshirt + White Pants + Converse

A sweatshirt paired with white pants and Converse sneakers makes for a cozy, stylish back-to-school outfit that’s perfect for casual comfort.

26. Fun Cardigan + White Flair Track Pants + Reebok Club C Sneakers

Pair a fun cardigan with white flair track pants for a playful yet chic look. Add Reebok Club C sneakers to complete this trendy and comfortable back-to-school outfit.

27. A-Line Jumper Dress + Baby Tee + Loafers

An A-line jumper dress over a baby tee creates a cute, layered style. Add loafers for a fashionable and comfortable look that’s perfect for any school day.

28. Embroidery Jacket + Sweater + White Pants + Mary Janes

An embroidery jacket layered over a sweater with white pants creates a chic look. Complete the outfit with Mary Janes for a stylish and polished ensemble.

29. Pullover Sweater + Wide Legged Jeans

A pullover sweater paired with wide-legged jeans creates a cozy and stylish look, perfect for a comfortable yet trendy back-to-school outfit.

Preppy Outfits for Back to School

For some schools, there is a strict dress code and that usually means preppy outfits are what they want.

So, stepping into the new school year with a preppy outfit can set the tone for a stylish and polished year.

Preppy fashion is all about classic, clean lines, and timeless pieces that exude an effortless elegance. Here are some ideas to help you achieve that perfect preppy look.

Start with a well-fitted blazer.

Whether it’s a navy blue, classic black, or even a bold plaid, a blazer can instantly elevate any outfit. Pair it with a crisp white button-down shirt or a classic striped tee for a sophisticated yet approachable look.

For bottoms, consider pleated skirts or tailored trousers.

A knee-length pleated skirt in a neutral color or plaid pattern paired with knee-high socks and loafers gives off a quintessentially preppy vibe.

Tailored trousers, on the other hand, offer a more modern take on preppy style. Opt for high-waisted cuts in neutral tones and pair them with a tucked-in blouse or a fitted sweater.

Sweaters are another key element of preppy fashion.

Think cable-knit, argyle, or simple V-neck sweaters layered over a collared shirt.

This layering not only adds dimension to your outfit but also keeps you warm during the cooler months.

Accessorize with classic pieces like a leather satchel, pearl earrings, or a simple headband.

These small touches can make a big difference in pulling together your preppy look.

Lastly, don’t forget about footwear.

Loafers, ballet flats, and classic sneakers are all excellent choices that complement the preppy style. Choose polished, comfortable shoes that will carry you through the school day with ease.

By mixing and matching these elements, you can create a variety of preppy outfits that are perfect for back to school.